ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles
A sustainable and atom-economic method was developed to prepare functionalized nitroalkyl pyrroles through a multicomponent reaction involving anilines, hexane-2,5-dione, and β-nitrostyrene derivatives. Ammonium niobium oxalate (ANO) was used as a cheap and reusable catalyst with ethanol as an eco-f...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-06-01
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| Series: | Tetrahedron Green Chem |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2773223124000256 |
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| author | Luiz H. Dapper Viviane T. Mena Márcio S. Silva Filipe Penteado Eder J. Lenardão |
| author_facet | Luiz H. Dapper Viviane T. Mena Márcio S. Silva Filipe Penteado Eder J. Lenardão |
| author_sort | Luiz H. Dapper |
| collection | DOAJ |
| description | A sustainable and atom-economic method was developed to prepare functionalized nitroalkyl pyrroles through a multicomponent reaction involving anilines, hexane-2,5-dione, and β-nitrostyrene derivatives. Ammonium niobium oxalate (ANO) was used as a cheap and reusable catalyst with ethanol as an eco-friendly solvent. A total of twenty-five N-substituted nitroalkyl-functionalized pyrroles were prepared in moderate to excellent yields (up to 93%). The method was successfully applied to electron-rich and electron-poor anilines, as well as to butylamine, simply by using a telescoping procedure (one-pot). Besides, the easy transformation of the obtained product in a primary amine was demonstrated. |
| format | Article |
| id | doaj-art-351e6c7be2164852abc8ddee9a9519f8 |
| institution | Kabale University |
| issn | 2773-2231 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Green Chem |
| spelling | doaj-art-351e6c7be2164852abc8ddee9a9519f82024-12-13T11:09:10ZengElsevierTetrahedron Green Chem2773-22312025-06-015100060ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrrolesLuiz H. Dapper0Viviane T. Mena1Márcio S. Silva2Filipe Penteado3Eder J. Lenardão4Centro de Ciências Químicas, Farmacêuticas e de Alimentos – CCQFA, Universidade Federal de Pelotas – UFPel, PO Box 354, 96010-900, Pelotas, RS, BrazilCentro de Ciências Químicas, Farmacêuticas e de Alimentos – CCQFA, Universidade Federal de Pelotas – UFPel, PO Box 354, 96010-900, Pelotas, RS, BrazilCentro de Ciências Químicas, Farmacêuticas e de Alimentos – CCQFA, Universidade Federal de Pelotas – UFPel, PO Box 354, 96010-900, Pelotas, RS, BrazilDepartamento de Química, Centro de Ciências Naturais e Exatas – CCNE, Universidade Federal de Santa Maria – UFSM, Av. Roraima, Building 18, 97105-900, Santa Maria, RS, Brazil; Corresponding author.Centro de Ciências Químicas, Farmacêuticas e de Alimentos – CCQFA, Universidade Federal de Pelotas – UFPel, PO Box 354, 96010-900, Pelotas, RS, Brazil; Corresponding author.A sustainable and atom-economic method was developed to prepare functionalized nitroalkyl pyrroles through a multicomponent reaction involving anilines, hexane-2,5-dione, and β-nitrostyrene derivatives. Ammonium niobium oxalate (ANO) was used as a cheap and reusable catalyst with ethanol as an eco-friendly solvent. A total of twenty-five N-substituted nitroalkyl-functionalized pyrroles were prepared in moderate to excellent yields (up to 93%). The method was successfully applied to electron-rich and electron-poor anilines, as well as to butylamine, simply by using a telescoping procedure (one-pot). Besides, the easy transformation of the obtained product in a primary amine was demonstrated.http://www.sciencedirect.com/science/article/pii/S2773223124000256Multicomponent reactionPaal-knorr synthesis3-Nitroalkyl-N-Substituted pyrrolesAmmonium niobium oxalate |
| spellingShingle | Luiz H. Dapper Viviane T. Mena Márcio S. Silva Filipe Penteado Eder J. Lenardão ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles Tetrahedron Green Chem Multicomponent reaction Paal-knorr synthesis 3-Nitroalkyl-N-Substituted pyrroles Ammonium niobium oxalate |
| title | ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles |
| title_full | ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles |
| title_fullStr | ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles |
| title_full_unstemmed | ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles |
| title_short | ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles |
| title_sort | ano catalyzed multicomponent synthesis of 3 nitroalkyl n substituted pyrroles |
| topic | Multicomponent reaction Paal-knorr synthesis 3-Nitroalkyl-N-Substituted pyrroles Ammonium niobium oxalate |
| url | http://www.sciencedirect.com/science/article/pii/S2773223124000256 |
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